Key West is compact, and yet plenty of visitors miss the best parts because they stick to Duval Street and Mallory Square.
One of the most scenic strolls in Key West — and a top freebie — is the harborwalk along the Key West Historic Seaport, also known as the Key West Bight.
From picturesque schooners to hungry tarpon to historic exhibits to the best happy hour specials in town, the Key West Historic Seaport has plenty to offer a visitor.
Key West Historic Seaport is your entryway to dozens of nautical adventures, too, including at least 20 sunset cruises, kayak and boat rentals, snorkeling and scuba outings, fishing charters and the wonderful day trip to Dry Tortugas National Park.
History of Key West Historic Seaport
The Key West Historic Seaport’s original name was Key West Bight. (A bight is a curve or bend in a shoreline or a loop in a rope.)
It first became an attraction to tourists in the 1940s for what we now find to be a rather sad reason – ships came here to unload boatloads of sea turtles for delivery to canning factories and people gathered to watch the spectacle.
The turtles – usually the rarer green turtles — were stacked on their backs and kept alive until they were butchered for processing. Shallow pens in the water called turtle crawls or kraals lined the seaport and canning factories hugged the waterfront.
The sea turtle population dwindled and finally sea turtles were protected in 1971. (Green turtles are still endangered species here.) What’s left of the turtle trade is the historic Turtle Kraals Restaurant and Bar on the site of the former Granday Turtle Cannery.
The best thing about the Turtle Kraals Restaurant? Its Tower Bar. This open-air roof bar has a spectacular unobstructed view of the harbor. It’s a great place to watch the sunset and see all the sunset cruises head out. Because it’s on the second floor, it’s easy to miss and thus folks feel like it’s their secret spot.
Three other enterprises kept the Key West Historic Seaport bustling during the 19th and 20th centuries – sponge fishing in the late 1800s (there were once 119 sponging vessels employing a thousand people); shrimping during the last half of the 20th Century (there were 500 shrimp boats pursuing “pink gold”) and commercial fishing.
In all cases, however, the story was the same: over-fishing, over-shrimping, over-sponging until supplies were nearly exhausted.
By 1992, turtle fishing and sponging were done and the remaining shrimping and commercial fishing boats had moved to cheaper harborage elsewhere in the Florida Keys.
Rather than allow the scenic harbor to decline into seediness or be taken over by a hotel or resort, the citizens agreed to have the city acquire it. Since then, Key West has preserved the flavor of the seaport, added historical markers and enhanced the walkway.
Highlights of Key West Historic Seaport
The best way to experience the seaport is to wander and linger. The harborwalk is about a mile along the water from Whiting Street to Front Street.
A few things to look for:
- Slow down and peer into the water. Huge tarpon hang out looking for handouts and manatees bob up occasionally. In front of Alonzo’s Oyster House at the foot of Front Street, tarpon are fed every day at 4 p.m.
Late in the afternoon when the fishing charters come back, it’s fun to see what they caught, watch workers filet the fish and fend off the ever-present pelicans.
- Happy hour in the harbor is widely celebrated and is a great bargain. We recommend Alonzo’s Oyster House, which has outdoor seating on the harbor and offers half priced drinks and appetizers from 5 to 6:30 p.m. every day. Their appetizer page includes clams and oysters, peel-and-eat shrimp, fish fingers as well as sides such as coleslaw and conch chowder. It’s easy to make this dinner, and it may be the best restaurant buy in Key West. Other harbor restaurants also have happy hour specials. Alonzo’s is at 700 Front St.
- Another popular half-price happy hour is at the Half Shell Raw Bar, 231 Margaret St. The Half Shell is iconic: worn-out bar stools, license-plate decor, a taxidermy sailfish on the wall. It’s such a classic that country music’s Kenny Chesney used a photo of it for the cover art to the single, “When I See This Bar,” off the album, “Life on a Rock.” Yelpers rave about the seafood quality and happy hour prices.
- There are always beautiful and historic boats in the harbor. One such beauty is the schooner Hindu, a 79-foot sailboat built in 1925. Hindu has had four names and as many roles over the years, including serving in World War II cruising for U-boats. After coming to Key West, its owner lost the boat to bank foreclosure and it fell into disrepair. In 2011, William Rowan bought “Hindu” from the bank and began restoration work. Hindu offers sunset and daytime sails in the winter in Key West and heads to Provincetown in the summer. Hindu is now joined by two other classic boats in the family.
Other tall ships include the two-masted Appledore Schooners II and V, which specialize in sunset cruises.
Sunset cruises from Key West Historic Seaport
If you are interested in a sunset cruise (and it’s a great way to enjoy a sunset), shop around. There are many variations on the theme.
Some are “all you can drink” cruises. The pirate-themed Jolly II Rover schooner is prominent with its jaunty red sails. Some cruises are on historic sailboats with champagne. Others are on catamaran party boats that critics say look like giant toaster ovens. Some are party boats with DJs and dancing; others are small and quiet.
Watch for promotions and discounts, though, as it is a competitive business.
Resources for a visit to Key West Historic Seaport
Sunset cruises and other boat outings from Key West Historic Seaport
- Classic Harbor Line for Beacon and America 2.0
- Jolly II Rover schooner
- Sunset Watersports
More things to do in Key West
- Free things to do in Key West
- Key West on a budget: Accommodations, restaurants
- Key West Butterfly Conservatory: A tranquil stop
- Audubon House, a lovely refuge in Key West
- Fort Zachary Taylor
- Hogfish Grill: Where Key West locals go for fresh fish
- Key West chickens
- Key West Tropical Forest and Botanic Garden: It will charm plant lovers
- Bike trail from Key West along Overseas Highway
- Authentic souvenirs in Key West
- Key West bars loved by locals
- Historic Key West cemetery
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The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.